Open AccessReaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage
Author(s) -
Yamamoto Yuki,
Sato Fumiya,
Kodama Shintaro,
Nomoto Akihiro,
Ogawa Akiya
Publication year - 2018
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/hc.21471
Subject(s) - chemistry , homolysis , telluride , reactivity (psychology) , aryl , bond cleavage , tellurium , radical , photochemistry , yield (engineering) , medicinal chemistry , substitution reaction , chalcogen , organic chemistry , catalysis , alkyl , medicine , alternative medicine , materials science , pathology , metallurgy
The reactivity of diaryl ditelluride and diaryl telluride toward aryl radicals was studied in detail. Diphenyl ditelluride underwent a bimolecular homolytic substitution (S H 2) reaction with a phenyl radical generated from phenylhydrazine in the air, to afford diphenyl telluride in excellent yield. Based on this diphenyl telluride synthesis, a one‐pot synthesis of unsymmetrical diaryl tellurides was developed by the S H 2 reaction of in situ generated diphenyl telluride with arylhydrazines in the air. The selectivity of mono‐/di‐substitution and the reactivity of arylhydrazines depend on the nature of the substituents on the arylhydrazines, that is, electron‐donating or ‐withdrawing group.